Ionically tagged iron complex-catalyzed epoxidation of olefins in imidazolium-based ionic liquids

ChemSusChem

Volumn 5, Issue 4, 2012, Pages 716-726

  Dos Santos, Marcelo R ^a,b   Diniz, Julia R ^a,b   Arouca, Aline M ^a,b   Gomes, Alexandre F ^c   Gozzo, Fabio C ^c   Tamborim, Silvia M ^d   Parize, Alexandre L ^a   Suarez, Paulo A Z ^a,b   Neto, Brenno A D ^a,b  

^a UNIVERSITY OF BRASILIA   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^c UNIVERSITY OF CAMPINAS   (Brazil)

^d UNIVERSIDADE FEDERAL DO PAMPA   (Brazil)

Author keywords

cytochromes; ionic liquids; iron; mass spectrometry; reaction mechanisms

Indexed keywords

CATALYSIS; ELECTROSPRAY IONIZATION; HYDROGEN PEROXIDE; IONIC LIQUIDS; IRON; MASS SPECTROMETRY; OLEFINS; OXIDATION; PROTEINS; SYNTHESIS (CHEMICAL);

AIR OXIDATION; CONCERTED MECHANISM; GOOD YIELD; IMIDAZOLIUM-BASED IONIC LIQUID; IRON-CATALYZED OXIDATIONS; OXIDATION REACTIONS; QUADRUPOLE-TIME OF FLIGHTS; REACTION CONDITIONS; REACTION MECHANISM;

IRON COMPOUNDS;

ALKENE; EPOXIDE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; IRON; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKENES; CATALYSIS; EPOXY COMPOUNDS; IMIDAZOLES; IONIC LIQUIDS; IRON; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION;

EID: 84859340691     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201100453     Document Type: Article

References (72)

1. K. M. Driller, H. Klein, R. Jackstell, M. Beller, Angew. Chem. 2009, 121, 6157-6160
2. Angew. Chem. Int. Ed. 2009, 48, 6041-6044.
3. G. Cahiez, S. Marquais, Pure Appl. Chem. 1996, 68, 53-60
4. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254
5. B. Plietker, in Iron Catalysis in Organic Chemistry (Ed.:, B. Plietker,), Wiley-VCH, Weinheim, 2008.
6. S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367
7. Angew. Chem. Int. Ed. 2008, 47, 3317-3321
8. A. Correa, O. Garcia Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117
9. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511
10. E. B. Bauer, Curr. Org. Chem. 2008, 12, 1341-1369
11. W. M. Czaplik, M. Mayer, J. Cvengros, A. Jacobi von Wangelin, ChemSusChem 2009, 2, 396-417.
12. R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282-2291
13. L. X. Liu, Curr. Org. Chem. 2010, 14, 1099-1126
14. W. M. Czaplik, M. Mayer, S. Grupe, A. Jacobi von Wangelin, Pure Appl. Chem. 2010, 82, 1545-1553
15. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293-1314
16. K. Junge, K. Schröder, M. Beller, Chem. Commun. 2011, 47, 4849-4859.
17. D. Ostovic, T. C. Bruice, Acc. Chem. Res. 1992, 25, 314-320
18. K. Schröder, X. Tong, B. Bitterlich, M. K. Tse, F. G. Gelalcha, A. Brückner, M. Beller, Tetrahedron Lett. 2007, 48, 6339-6342
19. K. Schröder, S. Enthaler, B. Bitterlich, T. Schulz, A. Spannenberg, M. K. Tse, K. Junge, M. Beller, Chem. Eur. J. 2009, 15, 5471-5481
20. G. Anilkumar, B. Bitterlich, F. G. Gelalcha, M. K. Tse, M. Beller, Chem. Commun. 2007, 289-291
21. K. Schröder, B. Join, A. J. Amali, K. Junge, X. Ribas, M. Costas, M. Beller, Angew. Chem. 2011, 123, 1461-1465
22. Angew. Chem. Int. Ed. 2011, 50, 1425-1429.
23. M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. L. de Laorden, R. Mas-Ballesté, M. Merz, L. Que, Jr. , Angew. Chem. 2006, 118, 3524-3528
24. Angew. Chem. Int. Ed. 2006, 45, 3446-3449
25. R. Mas-Ballesté, L. Que, Jr. , J. Am. Chem. Soc. 2007, 129, 15964-15972.
26. J. Bautz, P. Comba, C. L. de Laorden, M. Menzel, G. Rajaraman, Angew. Chem. 2007, 119, 8213-8216
27. Angew. Chem. Int. Ed. 2007, 46, 8067-8070
28. B. Bitterlich, G. Anilkumar, F. G. Gelalcha, B. Spilker, A. Grotevendt, R. Jackstell, M. K. Tse, M. Beller, Chem. Asian J. 2007, 2, 521-529
29. B. Bitterlich, K. Schröder, M. K. Tse, M. Beller, Eur. J. Org. Chem. 2008, 4867-4870
30. K. Schröder, S. Enthaler, B. Join, K. Junge, M. Beller, Adv. Synth. Catal. 2010, 352, 1771-1778
31. S. Taktak, W. Ye, A. M. Herrera, E. V. Rybak-Akimova, Inorg. Chem. 2007, 46, 2929-2942
32. G. Dubois, A. Murphy, T. D. P. Stack, Org. Lett. 2003, 5, 2469-2472
33. C. Marchi-Delapierre, A. Jorge-Robin, A. Thibon, S. Ménage, Chem. Commun. 2007, 1166-1168
34. K. Hasan, N. Brown, C. M. Kozak, Green Chem. 2011, 13, 1230-1237.
35. N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150.
36. J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3691.
37. J. Dupont, P. A. Z. Suarez, Phys. Chem. Chem. Phys. 2006, 8, 2441-2452.
38. J. Dupont, J. D. Scholten, Chem. Soc. Rev. 2010, 39, 1780-1804.
39. B. K. Sharma, K. M. Doll, S. Z. Erhan, Green Chem. 2007, 9, 469-474.
40. R. A. Pilli, L. G. Robello, N. S. Camilo, J. Dupont, A. A. M. Lapis, B. A. D. Neto, Tetrahedron Lett. 2006, 47, 1669-1672.
41. A. C. Pinto, A. A. M. Lapis, B. V. da Silva, R. S. Bastos, J. Dupont, B. A. D. Neto, Tetrahedron Lett. 2008, 49, 5639-5641.
42. A. A. M. Lapis, L. F. de Oliveira, B. A. D. Neto, J. Dupont, ChemSusChem 2008, 1, 759-762.
43. R. Bentley, Nat. Prod. Rep. 2006, 23, 1046-1062.
44. R. Šebesta, I. Kmentova, S. Toma, Green Chem. 2008, 10, 484-496.
45. F. A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, 4th ed., Wiley, New York, 1980, p. 152.
46. J. Dupont, J. Braz. Chem. Soc. 2004, 15, 341-350.
47. J. Dupont, J. Spencer, Angew. Chem. 2004, 116, 5408-5409
48. Angew. Chem. Int. Ed. 2004, 43, 5296-5297.
49. P. A. Z. Suarez, M. S. C. Pereira, K. M. Doll, B. K. Sharma, S. Z. Erhan, Ind. Eng. Chem. Res. 2009, 48, 3268-3270.
50. K. A. Srinivas, A. Kumar, S. M. S. Chauhan, Chem. Commun. 2002, 2456-2457.
51. U. Schröder, J. D. Wadhawan, R. G. Compton, F. Marken, P. A. Z. Suarez, C. S. Consorti, R. F. de Souza, J. Dupont, New J. Chem. 2000, 24, 1009-1015.
52. R. Rinaldi, F. Y. Fujiwara, W. Hölderich, U. Schuchardt, J. Catal. 2006, 244, 92-101.
53. R. G. Cesquini, J. M. S. Silva, C. B. Woitiski, D. Mandelli, R. Rinaldi, U. Schuchardt, Adv. Synth. Catal. 2002, 344, 911-914.
54. W. A. Lee, T. S. Calderwood, T. C. Bruice, Proc. Natl. Acad. Sci. USA 1985, 82, 4301-4305.
55. M. H. Lim, Y. J. Lee, Y. M. Goh, W. Nam, C. Kim, Bull. Chem. Soc. Jpn. 1999, 72, 707-713.
56. B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947-3980.
57. J. T. Groves, Y. Z. Han, in Cytochrome P450: Structure, Mechanism and Biochemistry (Ed.:, P. R. Ortiz de Montellano,), Plenum, New York, 1995, Chap. 1, p. 3.
58. N. A. Stephenson, A. T. Bell, J. Mol. Catal. A: Chem. 2007, 275, 54-62.
59. N. A. Stephenson, A. T. Bell, J. Am. Chem. Soc. 2005, 127, 8635-8643.
60. N. Hessenauer-Ilicheva, A. Franke, D. Meyer, W.-D. Woggon, R. van Eldik, Chem. Eur. J. 2009, 15, 2941-2959.
61. W. Nam, Y. O. Ryu, W. J. Song, J. Biol. Inorg. Chem. 2004, 9, 654-660.
62. J. T. Groves, Proc. Natl. Acad. Sci. USA 2003, 100, 3569-3574.
63. Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856.
64. S. Shaik, S. P. de Visser, D. Kumer, J. Biol. Inorg. Chem. 2004, 9, 661-668.
65. W. J. Song, Y. O. Ryu, R. Song, W. Nam, J. Biol. Inorg. Chem. 2005, 10, 294-304.
66. P. Comba, G. Rajaraman, Inorg. Chem. 2008, 47, 78-93.
67. P. Comba, M. Maurer, P. Vadivelu, Inorg. Chem. 2009, 48, 10389-10396.
68. D. Kumar, H. Hirao, S. P. de Visser, J. Zheng, D. Wang, W. Thiel, S. Shaik, J. Phys. Chem. B 2005, 109, 19946-19951.
69. K. Chen, M. Costas, J. Kim, A. K. Tipton, L. Que, Jr. , J. Am. Chem. Soc. 2002, 124, 3026-3035.
70. D. S. Choi, D. H. Kim, U. S. Shin, R. R. Deshmukh, S-g. Leeb, C. E. Song, Chem. Commun. 2007, 3467-3469.
71. S. Jain, M. P. Sharma, Renewable Sustainable Energy Rev. 2011, 15, 438-448.
72. S. Jain, M. P. Sharma, Renewable Sustainable Energy Rev. 2010, 14, 1937-1947.